Isomerization of 5-(2H-Azirin-2-yl)oxazoles: An Atom-Economic Approach to 4H-Pyrrolo[2,3-d]oxazoles
Keyword(s):
An atom economical method for the preparation of variously substituted 4H-pyrrolo[2,3-d]oxazoles was developed on the basis of thermal isomerization of 5-(2H-azirin-2-yl)oxazoles. The latter were prepared by Rh2(oct)4 catalyzed reaction of 2-(3-aryl/heteroaryl)-2-diazoacetyl-2H-azirines with a set of substituted acetonitriles, benzonitriles, acrylonitrile and fumaronitrile. According to DFT calculations the transformation of 5-(2H-azirin-2-yl)oxazole to 4H-pyrrolo[2,3-d]oxazole occurs through the nitrenoid-like transition state to give a 3aH-pyrrolo[2,3-d]oxazole intermediate, followed by 1,5-H-shift.
2019 ◽
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2005 ◽
Vol 340
(5)
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pp. 1051-1057
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2011 ◽
Vol 47
(2)
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pp. 93-100
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2007 ◽
Vol 31
(1)
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pp. 241-248
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2020 ◽
2005 ◽
pp. 859-873
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2019 ◽
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2019 ◽
2013 ◽
Vol 9
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pp. 1073-1082
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